Synthesis and Copper(II)-Complexation Properties of an Unusual Macrocyclic Structure Containing α/β-Amino Acids and Anomeric Sugar β-Amino Acid - Université de Lorraine Access content directly
Journal Articles European Journal of Organic Chemistry Year : 2013

Synthesis and Copper(II)-Complexation Properties of an Unusual Macrocyclic Structure Containing α/β-Amino Acids and Anomeric Sugar β-Amino Acid

Abstract

A 16-membered macrocycle containing histidine, β-alanine, and an anomeric sugar β-amino acid was synthesised using a stepwise procedure starting from an exo-glycal derivative. This new macrocyclic structure contains an unusual carbonic carbamic anhydride moiety that was spontaneously formed upon saponification of the C-terminus ester group by attack of the resulting carboxylate group on the N-terminal benzyloxycarbonyl protecting group. This macrocyclic ligand formed a 1:1 complex with copper(II) ions in aqueous solution at basic pH. A structural study of this complex in solution was undertaken by UV/Vis, and paramagnetic 1H and 13C NMR spectroscopy. These spectroscopic data strongly suggest a {3 × Namide, NIm} equatorial donor set around the copper(II) ion, the fourth amide nitrogen being inaccessible for coordination, probably due to the rigid structure imposed by the sugar unit and the anhydride moiety.

Dates and versions

hal-01524707 , version 1 (18-05-2017)

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Anne-Sophie Felten, Nadia Pellegrini-Moïse, Katalin Selmeczi, Benoît Henry, Yves Chapleur. Synthesis and Copper(II)-Complexation Properties of an Unusual Macrocyclic Structure Containing α/β-Amino Acids and Anomeric Sugar β-Amino Acid. European Journal of Organic Chemistry, 2013, 2013 (25), pp.5645 - 5654. ⟨10.1002/ejoc.201300454⟩. ⟨hal-01524707⟩
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